Enantioselective Construction of Axially Iodobenzocarbazole Derivatives by Stereogenic‐at‐Cobalt(III)‐Complex‐Catalyzed Iodoarylation of Alkynes DOI
Chuan‐Zhi Yao, Ziyuan Zhao,

Xue‐Qin Tu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(42)

Published: Sept. 7, 2023

Abstract A new synthetic approach to novel axially chiral iodobenzocarbazole derivatives based on the highly enantioselective intramolecular iodoarylation of linked alkyne‐indole systems was developed by using versatile catalyst, stereogenic‐at‐cobalt(III)‐complex, through an iodinated vinylidene o ‐quinone methide (IVQM) intermediate. This protocol provides 21 examples in excellent yields with good high enantioselectivities (up 96 % yield, 98 ee). Furthermore, introduced iodine atoms can easily be converted into other functional groups.

Language: Английский

Atroposelective Synthesis of 2‐Arylindoles via Chiral Phosphoric Acid‐Catalyzed Direct Amination of Indoles† DOI
Wen Bao, Ye‐Hui Chen, Yuwei Liu

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(7), P. 731 - 735

Published: Nov. 29, 2023

Comprehensive Summary Indole‐based atropisomers are a very important class of axially chiral compounds. However, the atroposelective synthesis 2‐arylindole remains largely unexplored. In this study, we report successful atropisomeric 2‐arylindoles using direct amination indoles with p ‐quinonediimines in presence phosphoric acid as catalyst. Quinonediimine acts an aminating reagent through formal polarity inversion imine. The malonate group on 2‐aryl 2‐indoles was found to be essential for high enantioselectivity products. This could due additional interaction between ester and catalyst, well intramolecular hydrogen bonding. Our findings provide new strategy asymmetric construction atropisomers.

Language: Английский

Citations

12
Research Progress on the Hydroamination of o-Alkynylanilines for the Synthesis of Axially Chiral Indoles DOI

Jiasheng Wang,

Ze‐Shu Wang, Wei‐Min He

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1786 - 1786

Published: Jan. 1, 2024

Language: Английский

Citations

2
Enantioselective Synthesis of Indole‐Derivated Axially Chiral Frameworks via CpXRh(III)‐Catalyzed Domino Cyclization/C3‐Arylation of 2‐Alkynylanilines with 1‐Diazonaphthoquinones DOI
Junwei Ye,

Qingwei Song,

Dongping Pan

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(5), P. 1064 - 1069

Published: Jan. 13, 2024

Abstract We report herein a chiral Cp X Rh(III)‐catalyzed domino cyclization/C 3 ‐arylation process using 2‐alkynylanilines and 1‐diazonaphthoquinones as viable substrates, delivering indole‐based derivatives endowed with axial chirality. The method features high enantioselectivity, broad substrate scope, robust functional group tolerance. Subsequent functionalization of the synthesized scaffolds underlines practicality this approach in design indole‐derivated axially frameworks, demonstrating its substantial promise synthetic medicinal chemistry applications.

Language: Английский

Citations

1
Recent advances in atroposelective synthesis of axially chiral heterobiaryl featuring indole frameworks DOI

Jinding Wei,

Minghong Zhu,

Bo Zhang

et al.

Tetrahedron, Journal Year: 2023, Volume and Issue: 149, P. 133716 - 133716

Published: Nov. 3, 2023

Language: Английский

Citations

3
Rhodium-Catalyzed Enantioselective Addition of Heteroarenium Salts Enabled by Nucleophilic Cyclization of 2-Alkynylanilines DOI
Yaling Huang, Zisong Qi, Xingwei Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8439 - 8444

Published: Nov. 20, 2023

Transition-metal-catalyzed cyclative coupling of 2-alkynylanilines provides a feasible routine for accessing functionalized indoles. Herein, rhodium-catalyzed highly enantioselective addition heteroarenium salts is presented, which enabled by the nucleophilic cyclization 2-alkynylanilines. It offers protocols to access enantioenriched indoles tethered 1,2-dihydropyridine and 1,2-dihydroquinoline motifs with excellent enantioselectivities.

Language: Английский

Citations

2
Chiral Brønsted Acid‐Catalyzed Asymmetric Reaction via Vinylidene Ortho‐Quinone Methides DOI
Xin‐Qi Zhu,

Hai‐Yu Yang,

Long‐Wu Ye

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(49)

Published: June 26, 2024

Vinylidene ortho-quinone methides (VQMs) have been proven to be versatile and crucial intermediates in the catalytic asymmetric reaction last decade, thus drawn considerable concentrations on account of practical application construction enantiomerically pure functional organic molecules. However, comparison well established chiral Brønsted base-catalyzed via VQMs, acid-catalyzed is rarely studied there no systematic summary date. In this review, we summarize recent advances VQMs according three types reactions: a) intermolecular nucleophilic addition VQMs; b) cycloaddition c) intramolecular cyclization VQMs. Finally, put forward remained challenges opportunities for potential breakthroughs area.

Language: Английский

Citations

0
Enantioselective Construction of Axially Iodobenzocarbazole Derivatives by Stereogenic‐at‐Cobalt(III)‐Complex‐Catalyzed Iodoarylation of Alkynes DOI
Chuan‐Zhi Yao, Ziyuan Zhao,

Xue‐Qin Tu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(42)

Published: Sept. 7, 2023

Abstract A new synthetic approach to novel axially chiral iodobenzocarbazole derivatives based on the highly enantioselective intramolecular iodoarylation of linked alkyne‐indole systems was developed by using versatile catalyst, stereogenic‐at‐cobalt(III)‐complex, through an iodinated vinylidene o ‐quinone methide (IVQM) intermediate. This protocol provides 21 examples in excellent yields with good high enantioselectivities (up 96 % yield, 98 ee). Furthermore, introduced iodine atoms can easily be converted into other functional groups.

Language: Английский

Citations

1